Werner zerweck



" Patented Nov. 3,1931

' '7 WERNER ZERWEGK, or FRANKIEORT-ON-THE-MAIN-FECHENHEIM, GERMANY, ASSIGNOR ,ro ennnnnnnmnrnnwonxs, mo or NEW YORK, N. Y., A CORPORATION or DELA- nnotwnfva'r nmsrurrs or amn nmnnneumo m snmns NoZ Drawing. Application ifiie a April as; .1929, Serial No. 358,1 1, and in Germany a riras, 192s.

The resent invention relates to brown vat dyestu s of the anthraquinone series, more a particularly to dyestuffs corresponding to he following general formula:

arr ea:

' rc'ep o po nd wherein X means halogen, a nitroor diazogroup, and treating the-'anthrylthioanthra- .quinone-Q-carboxyhc acid thus formed and corresponding to the general formula:

asi

402 wherein means the number 1 or 2, with an acidcondensing agent. By thisreaction at According to 'this assumption the new dyerown yat 'dyestufls are anthraoene wherein n means the number or'2. I

*The new dyestuffs produced by myprocess dye the vegetable fiber valuable-yellowishbrown shadesof a very good fastness.

'In order to further illustrate my invention the following examples are given the parts bein by weight and all temperatures in centi-- gra e degrees. But I wish it tobe understood that Iv'am not limited to the particular conditions or specific products mentioned therein.

21 parts of fi mercapto-anthracene, prepared, for instance, by reduction of Q-inercapto-anthra'quinone', 28,7parts of, l-chloro-anthraquinone-2-carboxylic acid, 13 parts of potassium hydroxide and 300 parts ofwater are boiled together under a reflux condenser for several hours while nitrogen is introduced into the mass. Then the reaction mass is diluted with hot water and .filtered. The

orange colored filtrate is acidified with hydrochloric acid.' j- I-(W-anthryhthio) -anthraquinone-2-carboxylic acid thus separated is filtered off, washedv until free from, acid and dried. jltdissolves'in, a'lkalis to orange solutions. Thec olor of its solution in concentrat ed sulfuric' aeid is red and becomes quickly brownish-olive. i

4.6 partsiof this 1'-'(2-anthryl-thio) -anthraquinone-Q-fcarboxylic acid are warmed with 3.1- parts of phosphorus pentachloride in parts of trichloro-benzene for about 3 hours on the water-bath. Then the mass is heated to about 200 for still a short time. After cooling the reaction product islfilter'ed off, washed with chloro-benzene and then with acetone and extracted at boiling temperature with a dilute. sodasolution. The new dyestuff thusobtained corresponds probably to the formula 7. It representsa dark brown powder soluble in concentrated sulfuric" acid with an olive tint anddyes cotton from a green hydrosulfite V vat yellowish-brown s'hades of a good fast I 1-chloro-anthraquinone-2-carboxylic acidis condensed in the same manner as described 111 Example 1 with'-2.6-dimercapto-anthracene.

j Thereby 2.6 -die(2 carboXy-1-anthra-quinlQf furic acid with a brownish-olive tint which latter quicklyfturns togreenish-gray;

l5 ;parts ofthis dicarboxylic, acid are cononyl-thio) -anthrac ene ,is -obtained which is,

when dry, an"or ange"power, soluble in allialies with an orange tint, in concentrated suldensedin QQO parts of trichloro-benzene with to 12.4: parts o fi= phosphorus pentachlOride ac.-

cording to Example 1;, The new dyestufi thus 1 obtained corresponds probably to the v for- 11 "Y 1 a red color. Ityields on cotton from a green warm hydrosulfite at aful'l yellowish-brown dy v r I claim: 7

As new the brownyatdye s u fi spt he'p oba le "g n fa ormu aanthria'cene 7 wherein n stands for'l or 2', which products are when dry dark-brown powders,'dyeing the egetable fiber from a greenish vat brownish shades of a very good fastness'.

2. As a new product, the vat dyestufi' of the probable formula: x

, which dyestufi s dissolves in concentrated sulfuric acid with an olivetint and dyes cotton from ,green hydro-,sulfite Vat yellowish- Q brown shades ofa good fastness. 3. As a newproduct, the vat dyestuff of the probable formula: i

whi hdy st ft-di vs lrii hcen rat c e1:

WERNER ZERWEGK.

v dissolves in concentrated sulfuricacid with" furio acid withfa'red color'and dyes cotton I Y Y from. ag e mwarm hy ros fite atrfull yellowi h-b n shaesoiagen fas ne s- Intestimony-whereof,I'aifix my signature. 

